Water → N,N-dibenzyl-N'-(2-methoxyphenyl)ethylenediamine

HRID 463720Notes

Reaction equation

HRID 463720 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][N:14]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])=O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>C1COCC1>[CH2:27]([N:14]([CH2:13][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:15][CH2:16][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 962WaterHCID 135605532-[bis(phenylmethyl)amino]-N-(2-methoxyphenyl)acetamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 20255245N,N-dibenzyl-N'-(2-methoxyphenyl)ethylenediamineYield 54.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred slurry of 11 g of lithium aluminum hydride in 250 ml anhydrous THF under nitrogen was added dropwise a solution of 43.6 g of 2-[bis(phenylmethyl)amino]-N-(2-methoxyphenyl)acetamide in 500 ml anhydrous tetrahydrofuran and stirred overnight at room temperature. After cooling to 0°, the mixture was treated cautiously in succession with 50 ml of water. The granular precipitate was separated by filtration and washed several times with methylene chloride. The filtrate was evaporated to dryness, the residue dissolved in ether and the organic phase extracted with 3N hydrochloric acid. the water phase was made alkaline with 3N sodium hydroxide and the base extracted with methylene chloride. The organic layer was washed with water, dried over magnesium sulfate and evaporated at reduced pressure. The crude syrup (36.9 g) was chromatographed on silica gel column packed in methylene chloride. Elution with methylene chloride provided N,N-dibenzyl-N'-(2-methoxyphenyl)ethylenediamine (22.8 g) in the form of an oil.

Workup

  1. temperatureAfter cooling to 0°
  2. customThe granular precipitate was separated by filtration
  3. washwashed several times with methylene chloride
  4. customThe filtrate was evaporated to dryness
  5. dissolutionthe residue dissolved in ether
  6. extractionthe organic phase extracted with 3N hydrochloric acid
  7. extractionthe base extracted with methylene chloride
  8. washThe organic layer was washed with water
  9. dry with materialdried over magnesium sulfate
  10. customevaporated at reduced pressure
  11. customThe crude syrup (36.9 g) was chromatographed on silica gel column
  12. washElution with methylene chloride

Sources & evidence

ORD record
ord-ea87c4f9eb334c1e9ba910205dd4bb50
Source dataset
uspto-grants-1985_10
Patent number
US04544657

Reaction notes

Loading…